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The 1969 festival was considerably larger and more popular than the previous year's. Dylan had been little heard of since his allegedly near-fatal motorcycle accident in July 1966. Shunning the Woodstock Festival, held near his home in upstate New York,[4][5] Dylan was initially reluctant to perform his comeback show on the little-known Isle of Wight. After weeks of negotiations, the Foulk brothers showed him a short film of the island's cultural and literary heritage; this appealed to Dylan's artistic sensibilities, as he was enthusiastic about combining a family holiday with a live performance in Tennyson country.[6] The family was scheduled to travel to Britain on the QE2 and nearly missed the gig completely when Dylan's son Jesse was hit by a cabin door and had to be hospitalised. He instead travelled by plane at the last minute.[7]

Four performances from this concert were included on Dylan's album Self Portrait (1970): "Like a Rolling Stone", "The Mighty Quinn (Quinn the Eskimo)", "Minstrel Boy" and "She Belongs to Me". His and the Bands set was also released in several countries on various bootleg records.[17]

The Who presented their standard set at that time, which included the rock opera Tommy, as they had recently released that album and were touring in support of it. The group had just returned from a tour of the United States, where they had performed at Woodstock about two weeks earlier. They opened with "Heaven and Hell", followed by "I Can't Explain", "Fortune Teller", "Young Man Blues", and then performed the opera nearly in full, finishing up with "Summertime Blues", "Shakin' All Over"/"Spoonful" and two tracks as the encore: "My Generation" and the finale of "Naked Eye".[20]